GB1426557A - Production of substituted monomalonate esters and their use in the production of alpha-carboxy penicillins and cephalosporins - Google Patents

Production of substituted monomalonate esters and their use in the production of alpha-carboxy penicillins and cephalosporins

Info

Publication number
GB1426557A
GB1426557A GB4593672A GB4593672A GB1426557A GB 1426557 A GB1426557 A GB 1426557A GB 4593672 A GB4593672 A GB 4593672A GB 4593672 A GB4593672 A GB 4593672A GB 1426557 A GB1426557 A GB 1426557A
Authority
GB
United Kingdom
Prior art keywords
ester
substituted
production
carboxy
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4593672A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB4593672A priority Critical patent/GB1426557A/en
Priority to BE136034A priority patent/BE805298A/en
Priority to DE19732348473 priority patent/DE2348473A1/en
Priority to FR7334471A priority patent/FR2202093B1/fr
Priority to SE7313478A priority patent/SE402774B/en
Priority to DK540573A priority patent/DK132409C/en
Priority to NL7313636A priority patent/NL7313636A/xx
Priority to CH1418173A priority patent/CH587275A5/xx
Priority to JP11109173A priority patent/JPS5745226B2/ja
Publication of GB1426557A publication Critical patent/GB1426557A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

1426557 Substituted mono-malonate esters; α-carboxy penicillins BEECHAM GROUP Ltd 10 Sept 1973 [5 Oct 1972] 45936/72 Heading C2C A process for the preparation of a substituted mono-malonate ester of the formula wherein R is an alkyl, cycloalkyl, aryl or aralkyl group which may be substituted, and R<SP>1</SP> is a heterocyclic group, comprises reacting a substituted acetate ester of the formula with an alkyl lithium compound R<SP>11</SP>Li, wherein R<SP>11</SP> is (C 1 -C 5 ) alkyl, in the presence of a secondary amine at a temperature of from - 5‹ to -85‹ C. and then treating the formed lithium ester enolate with CO 2 . The lithium ester enolate is preferably reacted in situ in an ether direct with solid CO 2 . Examples describe the preparation of compounds wherein R<SP>1</SP> is a furyl or thienyl group. α-Carboxy penicillins and α-carboxy cephalosporins can conveniently be prepared by coupling an ester of the invention or a reactive derivative thereof, e.g. the acyl chloride, with 6-amino penicillanic or 7-amino cephalosporanic acid or a derivative thereof and optionally de-esterifying the resulting ester.
GB4593672A 1972-10-05 1972-10-05 Production of substituted monomalonate esters and their use in the production of alpha-carboxy penicillins and cephalosporins Expired GB1426557A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB4593672A GB1426557A (en) 1972-10-05 1972-10-05 Production of substituted monomalonate esters and their use in the production of alpha-carboxy penicillins and cephalosporins
BE136034A BE805298A (en) 1972-10-05 1973-09-25 MONO-MALONATE PREPARATION PROCESS
DE19732348473 DE2348473A1 (en) 1972-10-05 1973-09-26 METHOD FOR MANUFACTURING SUBSTITUTED MALONIC ACID MONOESTERS AND THEIR USE FOR MANUFACTURING ALPHACARBOXYPENICILLIN OR CEPHALOSPORIN
FR7334471A FR2202093B1 (en) 1972-10-05 1973-09-26
SE7313478A SE402774B (en) 1972-10-05 1973-10-03 PROCEDURE FOR MAKING MONOESTERS OF 2-HETEROCYCLE-SUBSTITUTED MALONIC ACIDS
DK540573A DK132409C (en) 1972-10-05 1973-10-04 PROCEDURE FOR THE PREPARATION OF HETEROCYCLIC SUBSTITUTED DEMALONATES
NL7313636A NL7313636A (en) 1972-10-05 1973-10-04
CH1418173A CH587275A5 (en) 1972-10-05 1973-10-04
JP11109173A JPS5745226B2 (en) 1972-10-05 1973-10-04

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4593672A GB1426557A (en) 1972-10-05 1972-10-05 Production of substituted monomalonate esters and their use in the production of alpha-carboxy penicillins and cephalosporins

Publications (1)

Publication Number Publication Date
GB1426557A true GB1426557A (en) 1976-03-03

Family

ID=10439170

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4593672A Expired GB1426557A (en) 1972-10-05 1972-10-05 Production of substituted monomalonate esters and their use in the production of alpha-carboxy penicillins and cephalosporins

Country Status (9)

Country Link
JP (1) JPS5745226B2 (en)
BE (1) BE805298A (en)
CH (1) CH587275A5 (en)
DE (1) DE2348473A1 (en)
DK (1) DK132409C (en)
FR (1) FR2202093B1 (en)
GB (1) GB1426557A (en)
NL (1) NL7313636A (en)
SE (1) SE402774B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051457A2 (en) * 1980-11-03 1982-05-12 Eli Lilly And Company Process for preparation of substituted benzyl esters

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5481262A (en) * 1977-12-06 1979-06-28 Oce Andeno Bv Manufacture of 33thienylmaloic acid or its diester
JPH02142917U (en) * 1989-05-01 1990-12-04

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3651050A (en) * 1969-01-23 1972-03-21 Pfizer Acylation of 6-aminopenicillanic acid and 7-aminocephalosporanic acid

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051457A2 (en) * 1980-11-03 1982-05-12 Eli Lilly And Company Process for preparation of substituted benzyl esters
EP0051457A3 (en) * 1980-11-03 1982-09-15 Eli Lilly And Company Process for preparation of substituted benzyl esters

Also Published As

Publication number Publication date
DK132409B (en) 1975-12-01
FR2202093A1 (en) 1974-05-03
JPS5745226B2 (en) 1982-09-27
SE402774B (en) 1978-07-17
JPS4992061A (en) 1974-09-03
NL7313636A (en) 1974-04-09
CH587275A5 (en) 1977-04-29
BE805298A (en) 1974-03-25
DK132409C (en) 1976-05-03
FR2202093B1 (en) 1979-04-13
DE2348473A1 (en) 1974-04-18

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee